Water → HCID 59002866, compound

HRID 561165Notes

Reaction equation

HRID 561165 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:20]([O-])=O)[C:10]([F:19])=[C:11]([F:18])[C:12]=3[O:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:23])[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.O>CC(O)=O.[Fe]>[NH2:20][C:9]1[C:10]([F:19])=[C:11]([F:18])[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[C:13]2[C:8]=1[C:7](=[O:23])[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 962WaterHCID 59002975HCID 59002975, compound

Product 1

HCID 59002866HCID 59002866, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-isopropoxy-5-nitro-4-oxoquinoline-3-carboxylate (222 mg, 0.560 mmol) and iron powder (188 mg, 3.36 mmol) in AcOH (6 mL) was stirred at 90° C. for 5 h. After water was added, the reaction mixture was stirred for 30 min. The crude product was extracted with EtOAc, washed with saturated aq. NaHCO3 and brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1) to yield ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-isopropoxy-4-oxoquinoline-3-carboxylate (141 mg, 69%) as a pale yellow solid.

Workup

  1. stirringthe reaction mixture was stirred for 30 min
  2. extractionThe crude product was extracted with EtOAc
  3. washwashed with saturated aq. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1)

Sources & evidence

ORD record
ord-ef00b781f58643b783cb52946caa2a9d
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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